Xanthogen formates



Patented Aug. 26, 1952 XANTHOGEN FORMATES Arthur H. Fischer, New York,N. Y., assignor to Mmerec Corporation, New York, N. Y., a corporation ofNew York No Drawing. Application June 2, 1948, Serial No. 30,741

Claims.

q a 1 This invention relates to the production of new organic compoundsand has for an object the provision of novel xanthogen formates. Moreparticularly, the invention contemplates the provision of novel alkylxanthogen formates. An object of the invention is to provide xanthogenformates having a saturated alkyl radical as a substituent of thexanthogen moiety and a radical as a substituent of the formate moietywhich is more polar than an ethyl group would be if present as such asubstituent.

The reagents of the invention may be produced by reacting alkylxanthates comprising saturated alkyl radicals with chloroformatescomprising unsaturated organic radicals in accordance with the followingequation:

In the formulas set forth above, R is a saturated alkyl radicalcontaining not less than two carbon atoms and R is an unsaturatedorganic radical comprising a double bond or an unsaturated organicradical comprising a triple bond.

The compounds of the invention are suitable for various uses. They maybe employed with particular advantage as mineral collecting agents inthe concentration of minerals by froth flotation. Among the compoundsfound most suitable for use in such concentration processes are: ethylxanthogen allyl formate, ethyl xanthogen propargyl formate, ethylxanthogen methallyl formate, propyl xanthogen allyl formate. propylxanthogen propargyl formate, propyl xanthogen methallyl formate, butylxanthogen allyl formate, butyl xanthogen propargyl formate, butylxanthogen methallyl formate, amyl xanthogen allyl formate, amylxanthogen propargyl formate, amyl xanthogen methallyl formate, hexylxanthogen allyl formate, hexyl xanthogen propargyl formate, and hexylxanthogen methallyl formate.

Compounds of the above types may be illustrated by the followingstructural formulas:

HHH

t t i t in which R is a saturated alkyl radical containing from two tosix carbon atoms having as the substituent of the xanthogen moiety andin which an unsaturated allyl radical is having as the substituent ofthe formate moiety;

in which R is a saturated alkyl radical contain- 2 ing from two to sixcarbon atoms disposed on the xanthogen side and in which an unsaturatedmethallyl radical is disposed on the formate side; and

ROCSCO CEC-H i t i in which R is a saturated alkyl radical containingfrom two to six carbon atoms disposed on the xanthogen side and in whichan unsaturated propargyl radical is disposed on the formate side.

The use of the compounds of the invention for the concentration ofminerals is described and claimed in my copending application Serial No.30,742, filed June 2, 1948.

The following example illustrates a method of preparing compounds inaccordance with the invention:

60.2 grams of allyl chloroformate were added rapidly with constantstirring to a solution of 94.1 grams of potassium butyl xanthate in 400cc. of water at a temperature of about 25 C. The reaction proceededslowly with the production of an oily liquid product. After stirringthree hours, the oily product was separated, washed, and dried invacuum. The yield was 110.2 grams, equivalent to 94% of theoreticalyield in accordance with the following equation:

The oily product was substantially pure butyl xanthogen allyl formate,as indicated by the following data:

By Anal- Theoretiysis cal Percent sulfur 27. 27.

in which R is an alkyl radical containing from two to six carbon atomsand R is an unsaturated hydrocarbon radical containing not more thanfour carbon atoms.

2. A compound havingthe structural formulain whichR is an alkylradicalof the roup con; sisting of ethyl, 'propyl, butyl, amyl and hexyl, and Ris an unsaturated hydrocarbon radical containing not more than fourcarbon atoms.

3. A compound having the structural formula- HHH 4. A compound havingthe structural formula-- in which R is an alkyl radical of the group comsisting of ethyl, propyl, butyl, amyl, and hexyl.

5. A compound having the structural formulam WhichR is an alkylradicalor the group con sisting of ethyl, propyl, butyl, amyl, and hexyl.

ARTHUR H. FISCHER.

REFERENCES CITED 'Ih' following references are of record in the file ofthis patent:

UNITED STATES PATENTS Number Name Date 1,684,536 Fischer Sept. 18. 19281,796,972 Whitby Mar. 17, 1931 2,070,634 Werntz Feb. 16, 1937 2,368,670Lincoln et a1 Feb. 6, 1945 2,412,500 Fischer Dec. 10, 1946

1. A COMPOUND HAVING THE STRUCTURAL FORMULA-